US2023192665A1PendingUtilityA1
Organic electroluminescent materials and devices
Est. expiryDec 16, 2041(~15.4 yrs left)· nominal 20-yr term from priority
C07D 495/10H01L 51/0071H01L 51/0055C07D 487/06C07F 7/0812C07D 487/16H01L 51/50C07B 2200/05C07D 519/00H01L 51/0073C07D 493/10C07F 5/027C07D 403/14H01L 51/0074H01L 51/0067H01L 51/0072H01L 51/0094H10K 85/6576H10K 85/40H10K 85/654H10K 85/623H10K 85/6574H10K 85/6572H10K 85/657H10K 50/11H10K 2101/10C07F 5/02H10K 85/622H10K 85/342H10K 85/322
62
PatentIndex Score
0
Cited by
0
References
0
Claims
Abstract
Provided are compounds comprising a first moiety and a second moiety, wherein the first moiety comprises an azabenzene joined to a trivalent nitrogen atom that is part of an at least three-cyclic heteroaromatic ring system. Also provided are formulations comprising these compounds. Further provided are organic light emitting devices (OLEDs) and related consumer products that utilize these compounds.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound comprising a first moiety and a second moiety;
wherein the first moiety comprises an azabenzene joined to a trivalent nitrogen atom that is part of an at least three-cyclic heteroaromatic ring system; wherein the second moiety has a spherocity greater than or equal to 0.4; wherein the second moiety has a molecular weight greater than or equal to 250 g/mol.
2 . The compound of claim 1 , wherein the second moiety is not a tetraphenyl methyl, tetraphenyl silyl, or tetraphenyl germyl group.
3 . The compound of claim 1 , wherein the second moiety has a spherocity greater than or equal to
0 . 8.
4 . A compound comprising a first moiety and a second moiety, wherein the first moiety has Formula I:
wherein X 1 , X 2 , and X 3 are each independently C or N;
wherein at least one of X 1 , X 2 , and X 3 is N;
wherein R A , and R B are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein R 1 and R 2 are each independently a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein at least one of R 1 , R 2 R A , and R B comprises the second moiety selected from Formulae II, III, IV, V, VI and VII:
wherein rings A, B, and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein each X 5 -X 82 and X 201 -X 216 is independently C or N;
wherein Z 1 to Z 4 , and Y E are each independently a direct bond or selected from the group consisting of O, S, Se, NR, BR, BRR′, PR, CR, C═X, CRR′, SO, SO 2 , SiRR′, GeRR′, P(O)R,varyl, hetero aryl, alkyl, hetero cycloalkyl, and cycloalkyl;
wherein X is selected from the group consisting of O, S, and CRR′;
wherein W 1 and W 2 are each independently selected from the group consisting of O, S, Se, CRR′, SiRR′, and GeRR′;
wherein Z A is independently C, Si, or Ge;
wherein each R AA , R BB , R C , R D , R E , R F , R G , R H , R I , R J , R K , R L , R M , R N , R O , R P , R Q , R U , R V , R W , and R X represents mono to the maximum amount of substitution, or no substitution;
wherein R, R′, R AA , R BB , R C , R D , R E , R F , R G , R H , R I , R J , R K , R L , R M , R N , R O , R P , R Q , R U , R V , R W , and R X are each independently a hydrogen or a sub stituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein any two substituents may be joined or fused to form a ring, with the proviso that none of R N , R O , R P , and RQ are joined together to form a ring;
wherein if the compound has a structure of Formula VIII
wherein R 11 , R 12 , R 13 , and R 14 are each selected from the group consisting of aryl, heteroaryl, and combinations thereof, then R 5 is H or D;
provided that
(i) if the compound comprises a moiety according to Formula IV, and all of Z 1 -Z 4 are a direct bond, then none of X 8 and X 9 , or X 12 and X 13 , or X 16 and X 17 , or X 20 and X 5 are connected by a nitrogen to form a pyrrole ring;
(ii) if the compound comprises a moiety according to Formula IV, and all of Z 1 -Z 4 are a direct bond, then a benzimidazole moiety directly attached via its nitrogen atom to the central azabenzene moiety of Formula (I) does not share one of its carboxylic 6-membered aromatic rings with a carboxylic 6-membered aromatic ring of the moiety according to Formula IV.
5 . The compound of claim 4 , wherein the second moiety has a spherocity greater than or equal to 0.4.
6 . The compound of claim 4 , wherein the second moiety has a molecular weight greater than or equal to 250 g/mol.
7 . The compound of claim 4 , wherein at least one of R 1 , R 2 , R A , and R B comprises the second moiety of Formula II, and wherein ring A or ring B is a 6-membered carboxylic ring.
8 . The compound of claim 4 , wherein at least one of R 1 , R 2 , R A , and R B comprises the second moiety of Formula III, and wherein ring D is a 6-membered carboxylic ring.
9 . The compound of claim 4 , wherein at least one of R 1 , R 2 , R A , and R B comprises the second moiety of Formula IV, and wherein all R E -R H are hydrogen except of one which links the moiety of Formula IV to the structure of Formula I.
10 . The compound of claim 4 , wherein at least two of X 1 , X 2 , and X 3 are N.
11 . The compound of claim 4 , wherein the compound has Formula IX
wherein ring C is a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein X 4 is N or C; and
wherein X 1 , X 2 , and R A are as defined above.
12 . The compound of claim 4 , wherein at least one of R 1 , R 2 R A , R B comprises a moiety selected from the group consisting of:
13 . The compound of claim 4 , which is not
14 . The compound of claim 4 , wherein the compound is selected from the group consisting of:
wherein each X 83 -X 224 is independently C or N;
wherein L A1 is a direct bond or selected from the group consisting of O, S, Se, NR, BR, BRR′, PR, CR, C═X, CRR′, SO, SO 2 , SiRR′, GeRR′, P(O)R, aryl, hetero aryl, alkyl, hetero cycloalkyl, and cycloalkyl;
wherein each R CC , R R , R S , and R T represents mono to the maximum amount of substitution, or no substitution;
wherein R CC , R R , R S , and R T are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein any two substituents may be joined or fused to form a ring, with the proviso that none of R N , R O , R P , and R Q are joined together to form a ring.
15 . The compound of claim 14 , wherein L A1 is selected from the group consisting of direct bond, phenyl, pyridine, pyrimidine, triazine, carbazole and benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (bimbim).
16 . The compound of claim 14 , wherein at least one of X 4 to X 224 is N.
17 . The compound of claim 14 , wherein the compound is selected from the group consisting of:
Compound
Structure of compound
Compound 1-(Ro)(Rp)(Arl), wherein Compound 1- (R1)(R1)(Ar1) to Compound 1-(R17)(R135)(Ar27), have the structure
Compound 2-(Ro)(Rp)(Arl), wherein Compound 2- (R1)(R1)(Ar1) to Compound 2-(R17)(R135)(Ar27), have the structure
Compound 3-(Ro)(Rp)(Arl), wherein Compound 3- (R1)(R1)(Ar1) to Compound 3-(R17)(R135)(Ar27), have the structure
Compound 4-(Ro)(Rp)(Arl), wherein Compound 4- (R1)(R1)(Ar1) to Compound 4-(R17)(R135)(Ar27), have the structure
Compound 5-(Ro)(Rp)(Arl), wherein Compound 5- (R1)(R1)(Ar1) to Compound 5-(R17)(R135)(Ar27), have the structure
Compound 6-(Ro)(Rp)(Arl), wherein Compound 6- (R1)(R1)(Ar1) to Compound 6-(R17)(R135)(Ar27), have the structure
Compound 7-(Ro)(Rp)(Arl), wherein Compound 7- (R1)(R1)(Ar1) to Compound 7-(R17)(R135)(Ar27), have the structure
Compound 8-(Ro)(Arl)(Arm), wherein Compound 8- (R1)(Arl)(Ar1) to Compound 8-(R17)(Ar27)(Ar27), have the structure
Compound 9-(Ro)(Arl)(Arm), wherein Compound 9- (R1)(Arl)(Ar1) to Compound 9-(R17)(Ar27)(Ar27), have the structure
Compound 10-(Ro)(Arl)(Arm), wherein Compound 10- (R1)(Ar1)(Ar1) to Compound 10-(R17)(Ar27)(Ar27), have the structure
Compound 11-(Ro)(Arl)(Arm), wherein Compound 11- (R1)(Ar1)(Ar1) to Compound 11-(R17)(Ar27)(Ar27), have the structure
Compound 12-(Ro)(Arl)(Arm), wherein Compound 12- (R1)(Ar1)(Ar1) to Compound 12-(R17)(Ar27)(Ar27), have the structure
Compound 13-(Ro)(Arl)(Arm), wherein Compound 13- (R1)(Ar1)(Ar1) to Compound 13-(R17)(Ar27)(Ar27), have the structure
Compound 14-(Ro)(Arl)(Arm), wherein Compound 14- (R1)(Ar1)(Ar1) to Compound 14-(R17)(Ar27)(Ar27), have the structure
Compound 15-(Ro)(Rp)(Arl), wherein Compound 15- (R1)(R1)(Ar1) to Compound 15-(R17)(R135)(Ar27), have the structure
Compound 16-(Ro)(Rp)(Arl), wherein Compound 16- (R1)(R1)(Ar1) to Compound 16-(R17)(R135)(Ar27), have the structure
Compound 17-(Rp)(Rq)(Arl), wherein Compound 17- (R1)(R1)(Ar1) to Compound 17-(R135)(R135)(Ar27), have the structure
Compound 18-(Rp)(Rq)(Arl), wherein Compound 18- (R1)(R1)(Ar1) to Compound 18-(R135)(R135)(Ar27), have the structure
Compound 19-(Rp)(Rq)(Arl), wherein Compound 19- (R1)(R1)(Ar1) to Compound 19-(R135)(R135)(Ar27), have the structure
Compound 20-(Rp)(Rq)(Arl), wherein Compound 20- (R1)(R1)(Ar1) to Compound 20-(R135)(R135)(Ar27), have the structure
Compound 21-(Rp)(Rq)(Arl), wherein Compound 21- (R1)(R1)(Ar1) to Compound 21-(R135)(R135)(Ar27), have the structure
Compound 22-(Rp)(Rq)(Arl), wherein Compound 22- (R1)(R1)(Ar1) to Compound 22-(R135)(R135)(Ar27), have the structure
Compound 23-(Rp)(Rq)(Arl), wherein Compound 23- (R1)(R1)(Ar1) to Compound 23-(R135)(R135)(Ar27), have the structure
Compound 24-(Rp)(Rq)(Arl), wherein Compound 24- (R1)(R1)(Ar1) to Compound 24-(R135)(R135)(Ar27), have the structure
Compound 25-(Rp)(Rq)(Arl), wherein Compound 25- (R1)(R1)(Ar1) to Compound 25-(R135)(R135)(Ar27), have the structure
Compound 26-(Rp)(Rq)(Arl), wherein Compound 26- (R1)(R1)(Ar1) to Compound 26-(R135)(R135)(Ar27), have the structure
Compound 27-(Rp)(Rq)(Arl), wherein Compound 27- (R1)(R1)(Ar1) to Compound 27-(R135)(R135)(Ar27), have the structure
wherein o is an integer from 1 to 17 and p and q are each independently an integer from 1 to 135, and 1 and k are each indepenently an integer from 1 to 27, and
wherein R1 to R135 are as defined as follows:
Structure
R1
R2
R3
R4
R5
R6
R7
R8
R9
R10
R11
R12
R13
R14
R15
R16
R17
R18
R19
R20
R21
R22
R23
R24
R25
R26
R27
R28
R29
R30
R31
R32
R33
R34
R35
R36
R37
R38
R39
R40
R41
R42
R43
R44
R45
R46
R47
R48
R49
R50
R51
R52
R53
R54
R55
R56
R57
R58
R59
R60
R61
R62
R63
R64
R65
R66
R67
R68
R69
R70
R71
R72
R73
R74
R75
R76
R77
R78
R79
R80
R81
R82
R83
R84
R85
R86
R87
R88
R89
R90
R91
R92
R93
R94
R95
R96
R97
R98
R99
R100
R101
R102
R103
R104
R105
R106
R107
R108
R109
R110
R111
R112
R113
R114
R115
R116
R117
R118
R119
R120
R121
R122
R123
R124
R125
R126
R127
R128
R129
R130
R131
R132
R133
R134
R135
wherein Ar1 to Ar27 are defined as follows:
Structure
Ar 1
Ar 2
Ar 3
Ar 4
Ar 5
Ar 6
Ar 7
Ar 8
Ar 9
Ar 10
Ar 11
Ar 12
Ar 13
Ar 14
Ar 15
Ar 16
Ar 17
Ar 18
Ar 19
Ar 20
Ar 21
Ar 22
Ar 23
Ar 24
Ar 25
Ar 26
Ar 27
18 . The compound of claim 4 , wherein the compound is selected from the group consisting of:
19 . An organic light emitting device (OLED) comprising:
an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a first moiety and a second moiety, wherein the first moiety has Formula I:
wherein X 1 , X 2 , and X 3 are each independently C or N;
wherein at least one of X 1 , X 2 , and X 3 is N;
wherein R A , and R B are each independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein R 1 and R 2 are each independently a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein at least one of R 1 , R 2 R A , and R B comprises the second moiety selected from Formulae II, III, IV, V, VI and VII:
wherein rings A, B, and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;
wherein each X 5 -X 82 and X 201 -X 216 is independently C or N;
wherein Z 1 to Z 4 , and Y E are each independently a direct bond or selected from the group consisting of O, S, Se, NR, BR, BRR′, PR, CR, C═X, CRR′, SO, SO 2 , SiRR′, GeRR′, P(O)R,varyl, hetero aryl, alkyl, hetero cycloalkyl, and cycloalkyl;
wherein X is selected from the group consisting of O, S, and CRR′;
wherein W 1 and W 2 are each independently selected from the group consisting of O, S, Se, CRR′, SiRR′, and GeRR′;
wherein Z A is independently C, Si, or Ge;
wherein each R AA , R BB , R C , R D , R E , R F , R G , R H , R I , R J , R K , R L , R M , R N , R O , R P , R Q , R U , R V , R W , and R X represents mono to the maximum amount of substitution, or no substitution;
wherein each R AA , R BB , R C , R D , R E , R F , R G , R H , R I , R J , R K , R L , R M , R N , R O , R P , R Q , R U , R V , R W , and R X are each independently a hydrogen or a sub stituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein any two substituents may be joined or fused to form a ring, with the proviso that none of R N , R O , R P , and R Q are joined together to form a ring;
wherein if the compound has a structure of Formula VIII
wherein R 11 , R 12 , R 13 , and R 14 are each selected from the group consisting of aryl, heteroaryl, and combinations thereof, then R 5 is H or D;
provided that
if the compound comprises a moiety according to Formula IV, and all of Z 1 -Z 4 are a direct bond, then none of X 8 and X 9 , or X 12 and X 13 , or X 16 and X 17 , or X 20 and X 5 are connected by a nitrogen to form a pyrrole ring;
(ii) if the compound comprises a moiety according to Formula IV, and all of Z 1 -Z 4 are a direct bond, then a benzimidazole moiety directly attached via its nitrogen atom to the central azabenzene moiety of Formula (I) does not share one of its carboxylic 6-membered aromatic rings with a carboxylic 6-membered aromatic ring of the moiety according to Formula IV.
20 . A consumer product comprising an organic light-emitting device (OLED) comprising:
an anode; a cathode; and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound of claim 4 .Join the waitlist — get patent alerts
Track US2023192665A1 — get alerts on status changes and closely related new filings.
We store only your email — no account needed. See our privacy policy.